- PROCESS FOR THE DIRECT ALPHA-METHYLENATION OF KETONES
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The invention relates to a process for preparing an α-methylene ketone comprising the step of reacting a ketone with formaldehyde in the presence of a catalyst which is an organic compound comprising at least one acid function or the corresponding salt, ester or amide thereof and at least one amine function or the corresponding ammonium salt, or a zwitterion thereof.
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Page/Page column 16; 17
(2020/06/10)
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- Enantio- And Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis
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The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxa
- Wada, Yuuki,Murata, Ryuichi,Fujii, Yuki,Asano, Keisuke,Matsubara, Seijiro
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p. 4710 - 4715
(2020/07/06)
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- Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition
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A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary-tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
- Cheng, Shuanghua,Yu, Shouyun
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p. 8607 - 8610
(2014/12/10)
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- Oxygen as single oxidant for two steps: Base-free one-pot Pd(ii)-catalyzed alcohol oxidation & arylation to halogen-intact β-aryl α,β-enones
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Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is
- Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu
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p. 45490 - 45494
(2014/12/10)
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- Additional vinyl ketones and their pyranyl ketones in gonyleptid harvestmen (Arachnida: Opiliones) suggest these metabolites are widespread in this family
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Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and 1H NMR. All of these species release vinyl ketones, and three of them produce the corresponding pyranyl ketones, which are presumed hetero-Diels-Alder (HDA) dimers. The vinyl ketones 5-methyl-1-hexen-3-one, rac-4-methyl-1-hexen-3-one, and (S)-4-methyl-1-hexen-3-one were synthesized. Natural 4-methyl-1-hexen-3-one is present as a single stereoisomer and has the R-configuration. Vinyl ketone dimers (HDA dimers) were also observed in the scent gland exudate and characterized by HRMS, 13C NMR, and 1H NMR chemical shifts of the pyranyl moiety.
- Wouters, Felipe C.,Rocha, Daniele F. O.,Goncalves, Caroline C. S.,MacHado, Glauco,Marsaioli, Anita J.
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p. 1559 - 1564
(2013/10/22)
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- Modular preparation of diverse dipyrrolemethanes
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A modular synthesis of polyfunctional dipyrrolemethanes is presented. Diverse side chains are introduced to 2-carboxypyrrole building blocks in two to four steps, resulting in a collection of substituted pyrroles that, when condensed in one step, give ris
- Pham, Cindy C.,Park, Michelle H.,Pham, Jenny Y.,Martin, Sadie G.,Schramm, Michael P.
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p. 1165 - 1173
(2013/06/05)
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- Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP2 and EP4 receptors agonists
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Replacement of the hydroxy cyclopentanone ring in PGE2 with chemically more stable heterocyclic rings and substitution of the unsaturated α-alkenyl chain with a metabolically more stable phenethyl chain led to the development of potent and selective analogs of PGE2. Compound 10f showed the highest potency and selectivity for EP4 the receptor.
- Zhao, Zhong,Araldi, Gian Luca,Xiao, Yufang,Reddy, Adulla P.,Liao, Yihua,Karra, Srinivasa,Brugger, Nadia,Fischer, David,Palmer, Elizabeth
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p. 6572 - 6575
(2008/09/16)
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- Dissociated nonsteroidal glucocorticoid receptor modulators; discovery of the agonist trigger in a tetrahydronaphthalene-benzoxazine series
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The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay (representing transrepression effects) over an MMTV GR agonist assay (representing transactivation effects). 52 and 60 have NFkB pIC50 = 8.92 (105%) and 8.69 (92%) and MMTV pEC50 = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.
- Barker, Mike,Clackers, Margaret,Copley, Royston,Demaine, Derek A.,Humphreys, Davina,Inglis, Graham G. A.,Johnston, Michael J.,Jones, Haydn T.,Haase, Michael V.,House, David,Loiseau, Richard,Nisbet, Lesley,Pacquet, Francois,Skone, Philip A.,Shanahan, Stephen E.,Tape, Dan,Vinader, Victoria M.,Washington, Melanie,Uings, Iain,Upton, Richard,McLay, Iain M.,Macdonald, Simon J. F.
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p. 4216 - 4231
(2007/10/03)
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- 2,3-BENZOXAZIN DERIVATIVES AS NON-STEROIDAL GLUCOCORTICOID RECEPTOR MODULATORS
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The present invention provides compounds of formula (I), wherein R1 represents 1-ethylpropyl, 1-methylethyl or 2-methylpropyl; or a physiologically functional derivative thereof; pharmaceutical compositions comprising the compounds, the use of
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Page/Page column 37
(2010/02/15)
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- Synthesis of vinyl and β-phthalimido ketones
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Vinyl ketones are prepared by reaction of an aldehyde with a vinyl Grignard reagent followed by a Swern oxidation. β-Phthalimido ketones are then obtained by 1,4-addition of phthalimide.
- Hammen,Braisted,Northrup
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p. 2157 - 2163
(2007/10/02)
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- Process for preparation of adjacently disubstituted ketones
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A novel 7-hydroxyprostaglandin E1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: STR1 wherein R8 represents H, CH3 or C2 H5, R9 represents H or CH3, R10 and R11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an α,β-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.
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